Upcoming 5K Races Near Pleasant Valley, NY

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8th Annual 5k Walk/Run for Overdose Awareness

Shelton, CT

Thursday, June 25th, 2026

View details for race 8th Annual 5k Walk/Run for Overdose Awareness

The Club 2nd Annual 5k!

Naugatuck, CT

Saturday, June 27th, 2026

View details for race The Club 2nd Annual 5k!

Westport Road Runners Summer Series

Westport, CT

Saturday, June 27th, 2026

1 Mile

15K

View details for race Westport Road Runners Summer Series

EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

View details for race EDRRC - Pawling Moonlight Trail Run 5K

Tunnel to Towers 5K Run & Walk - Bethel, CT

Bethel, CT

Sunday, June 28th, 2026

Fast

View details for race Tunnel to Towers 5K Run & Walk - Bethel, CT

Fork In The Trail 5k Presented By Peace, Love, ...

Bedford, NY

Sunday, June 28th, 2026

Trail

View details for race Fork In The Trail 5k Presented By Peace, Love, Trails

Fleet Feet Poughkeepsie's 2026 Pride Fun Run to...

Poughkeepsie, NY

Sunday, June 28th, 2026

View details for race Fleet Feet Poughkeepsie's 2026 Pride Fun Run to Benefit Dutchess Pride Center

Fleet Feet Poughkeepsie's 2026 Red, White & Bre...

Newburgh, NY

Friday, July 3rd, 2026

View details for race Fleet Feet Poughkeepsie's 2026 Red, White & Brew 5K Sponsored by ASICS

2026 Great American Weekend 5k/10k Goshen Rotar...

Goshen, NY

Saturday, July 4th, 2026

10K

View details for race 2026 Great American Weekend 5k/10k Goshen Rotary Run

Saugerties Independence Day 5K

Saugerties , NY

Saturday, July 4th, 2026

View details for race Saugerties Independence Day 5K

EDRRC - Racing to Save Lives 5K/10K

Lagrangeville, NY

Sunday, July 5th, 2026

10K

Trail

View details for race EDRRC - Racing to Save Lives 5K/10K

Roxbury Road Race Series #18

Roxbury, CT

Saturday, July 11th, 2026

View details for race Roxbury Road Race Series #18

The 39th Annual Women's Distance Festival 5K

Congers, NY

Sunday, July 12th, 2026

View details for race The 39th Annual Women's Distance Festival 5K

Petit Family Foundation 5K

Plainville, CT

Sunday, July 12th, 2026

View details for race Petit Family Foundation 5K

PATTERSONS PELLET—53rd Summer Series Week Two

Kerhonkson, NY

Monday, July 13th, 2026

1 Mile

Trail

View details for race PATTERSONS PELLET—53rd Summer Series Week Two

Ambulance Driver 5K ...

Derby, CT

Wednesday, July 15th, 2026

View details for race Ambulance Driver 5K at BADSONS Brewery

Annual 5K Gardiner Classic Run/Walk

Gardiner, NY

Thursday, July 16th, 2026

Trail

View details for race Annual 5K Gardiner Classic Run/Walk

Fleet Feet Poughkeepsie's Ice Cream Fun Run

Poughkeepsie, NY

Monday, July 20th, 2026

View details for race Fleet Feet Poughkeepsie's Ice Cream Fun Run

Southwest Cafe Margarita 5K

Ridgefield, CT

Saturday, July 25th, 2026

View details for race Southwest Cafe Margarita 5K

New Milford Parks & Recreation Road Race

New Milford, CT

Saturday, July 25th, 2026

View details for race New Milford Parks & Recreation Road Race

The Trumbull Rotary Sunset 5k Run & Walk

Trumbull, CT

Friday, July 31st, 2026

1 Mile

View details for race The Trumbull Rotary Sunset 5k Run & Walk

It's All Downhill From Here 5K

Wilton, CT

Saturday, August 1st, 2026

Trail

View details for race It's All Downhill From Here 5K

Monster Classic 5K & 10K Road Races

Monticello, NY

Sunday, August 2nd, 2026

10K

View details for race Monster Classic 5K & 10K Road Races

The Perogie Dash

Danbury, CT

Saturday, August 8th, 2026

View details for race The Perogie Dash

The Robert Van Tassel “Live the Dash” Memorial ...

Chelsea, NY

Sunday, August 9th, 2026

1 Mile

View details for race The Robert Van Tassel “Live the Dash” Memorial 5k sponsored by Chelsea Fire Company

Jill's Race for MS

Beacon Falls, CT

Saturday, August 15th, 2026

View details for race Jill's Race for MS

Millbrook Vineyards Wine Run 5k

Millbrook, NY

Sunday, August 16th, 2026

1 Mile

View details for race Millbrook Vineyards Wine Run 5k

Guess Your Time 2.5 mile Race

Yorktown Heights, NY

Wednesday, August 19th, 2026

View details for race Guess Your Time 2.5 mile Race

Amber Room Run from the Sun 5K

Danbury, CT

Thursday, August 20th, 2026

View details for race Amber Room Run from the Sun 5K

Trot For Trauma

Montgomery, NY

Saturday, August 22nd, 2026

View details for race Trot For Trauma

Storm King Run 2026

Highland Falls, NY

Sunday, August 23rd, 2026

1 Mile

10K

View details for race Storm King Run 2026

2026 Unite to Fight 5K Run/Walk

Stamford, CT

Sunday, August 23rd, 2026

View details for race 2026 Unite to Fight 5K Run/Walk

1st Annual Newtown Community Running Event

Newtown, CT

Sunday, August 30th, 2026

10K

Half

View details for race 1st Annual Newtown Community Running Event

Lobster Loop 5K

Canton, CT

Sunday, August 30th, 2026

View details for race Lobster Loop 5K

Black Hog Brewing Co. 5K Road Race

Oxford, CT

Saturday, September 5th, 2026

View details for race Black Hog Brewing Co. 5K Road Race

Book It for the Olive Free Library 5K Run/Walk

Olivebridge, NY

Saturday, September 5th, 2026

View details for race Book It for the Olive Free Library 5K Run/Walk

2026 Ossining MATTERS Run-Walk for Education Fu...

Ossining, NY

Saturday, September 5th, 2026

View details for race 2026 Ossining MATTERS Run-Walk for Education Fundraiser

Warwick Lions Club Annual Labor Day 5K & 5 MIle...

Warwick, NY

Monday, September 7th, 2026

View details for race Warwick Lions Club Annual Labor Day 5K & 5 MIle Road Race and Kids Fun Run